Norethindrone Acetate

ID: ALA4091490

Cas Number: 38673-38-0

PubChem CID: 63021

Max Phase: Preclinical

Molecular Formula: C22H28O3

Molecular Weight: 340.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#C[C@@]1(OC(C)=O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22+/m0/s1

Standard InChI Key:  IMONTRJLAWHYGT-REGVOWLASA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   12.6436  -12.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6436  -13.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5141  -14.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9361  -13.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2239  -13.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5141  -13.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7943  -14.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9337  -12.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2140  -12.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9478  -14.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7863  -13.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2380  -14.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0832  -14.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3686  -14.9761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0844  -13.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4986  -11.6785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2239  -14.1481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5141  -12.9110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9361  -12.8929    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6436  -14.1382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4310  -13.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9174  -12.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4310  -12.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2162  -11.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0055  -10.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1456  -11.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8561  -12.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5708  -11.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8561  -13.0564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 12  1  0
  4  2  1  0
  5  4  1  0
  6  5  1  0
  7  3  2  0
  8  1  1  0
  9  8  1  0
 10  4  1  0
 11  6  1  0
 12 10  1  0
 13  7  1  0
 14 13  2  0
 15 11  1  0
  1 16  1  1
  5 17  1  6
  6 18  1  1
  4 19  1  1
  2 20  1  6
  9  5  1  0
  3  6  1  0
 13 15  1  0
  2 21  1  0
 21 22  1  0
 22 23  1  0
 23  1  1  0
 23 24  1  1
 24 25  3  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091490

   Norlutate

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 340.46

Molecular Weight (Monoisotopic): 340.2038

AlogP: 4.06

#Rotatable Bonds: 1

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: 1.97

References

1. Morgan RE, van Staden CJ, Chen Y, Kalyanaraman N, Kalanzi J, Dunn RT, Afshari CA, Hamadeh HK..  (2013)  A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.,  136  (1): [PMID:23956101] [10.1093/toxsci/kft176]

2. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

Source

Source(1):

• Scientific Literature